See Hatsie Travel

Travel: My Essential Guide to Boston


I often get asked to share recommendations for Boston.  It’s such an incredible city and one which holds a very special place in my heart, so I’m always thrilled to share what I think are must-sees in Boston.

Of course what I like may not be what you like, but I think these recommendations will definitely point you in the right direction, whether you are visiting for the weekend, or packing your bags and moving, like I did five years ago.

My Essential Guide to Boston

Boston is a city of neighborhoods. It’s the perfect walking city and even though it’s a big city, because of it’s neighborhoods, it feels like a small town. I think you could do nothing but walk in Boston and feel like you’ve been somewhere.  Because of this, it makes sense to me to organize my tips into neighborhoods.

  • Back Bay: My old neighborhood!  It’s a nice area with a mix of shops and restaurants and residential brownstones.  I used to live on Marlborough Street which claims to be the most beautiful street in Boston, although I am biased.
    • Things to Eat: Joe’s American Bar and Grill–really good American food—the steak tips are dreamy!  Charlie’s Saloon–Delicious French onion soup!  Parish Café–Holy sandwiches!  My all time favorite here is the meatloaf club. I dream about it. The Zuni Wrap is a fan favorite as well. Casa Romero– Located literally in an alley, you’ll miss it if you’re not looking for it.  Delicious Mexican food, great atmosphere.  You’ll definitely be with locals.  Stephanie’s on Newbury–Outdoors seating with a Parisian feel; great people watching.  The Globe–A neighborhood haunt that we would frequent often.  It was the first place I got a glass of wine when I visited Boston my senior year of college.
    • Things to See:  Top of the Hub/Prudential Tower–The second tallest building in Boston—you can catch some great views.  Boston Common and Boston Public Gardens–Beautiful parks with lots of space to stretch out.  Go ice skating in the winter!  Newbury Street–great shopping, better people watching.  Boston Public Library–Located in Copley Square, it’s a beautiful building.  The Esplanade–Green space that runs the length of the Charles river.  My favorite place to walk in Boston.
  • Beacon Hill: One of the oldest neighborhoods in Boston.  Charles Street is my favorite street in Boston. It has European charm and great little antique stores and shops to stop into. The winding streets are great for walking, especially if you want to sneak in some exercise. Those hills are no joke!
    • Things to Eat:  Il Grotto– it’s down in a little basement and feels delightfully authentic, charming, and cozy. 75 Chestnut–wonderful cocktails and appetizers.  Reservations are a must, but if you can grab a seat at the bar, it’s great too!
    • Things to See: The beautiful streets, hills, and architecture are worth the trip alone.  The Liberty Hotel is a converted jail and a fun place to stop for happy hour.
  • Waterfront: It overlooks the Harbor and is connected to both the North End and Faneuil Hall areas.
    • Things to Eat:  The Boston Sail Loft–My all time favorite place to get seafood in Boston.
    • Things to See:  The New England Aquarium.  See the seals!
  • North End: Boston’s “Little Italy,” it’s full of Italian restaurants and cafes. Hanover Street is the heart of the action, but I like Salem Street as well.
    • Things to Eat:  Bacco–On Salem Street, it’s a little off the tourist’s beaten path. They have a risotto of the day that is always good and the pasta is freshly made.  Mike’s Pastry–Famous for it’s Italian pastries—you’ll probably have to wait in a line.  Bova’s–24 hour bakery.  Obviously.
    • Things to See: The Freedom Trail (starts in the North End)–A trail marked by a painted red line all through the city that will take you past pretty much every historical attraction. It’s a hike so wear comfortable shoes.  Old North Church–Where Paul Revere lit the torches!
  • Faneuil Hall: A plaza of sorts with lots of restaurants and bars. This is where I went out every Friday and Saturday for maybe the first two years I lived in Boston.
    • Things to Eat:  Union Oyster House–The oldest, longest-running restaurant in the United States!  The clam chowder is amazing, as is the cornbread.  The Black Rose–a pretty authentic Irish pub complete with Irish music and Irish patrons!
    • Things to See: Quincy Market–Many a famous speech was given here.  there’s a great food court too.  The Rose Kennedy Greenway–Beautiful green space with art installations.  Take a picnice there.
  • Fenway:  Well, Redsox, obviously! The ballpark is definitely worth seeing. They do tours that are a lot of fun. There are great bars and restaurants around Fenway too.
    • Things to Eat: Boston Beer Works–casual atmosphere, they brew their own beer, and they have awesome fish and chips.  Cask and Flagon–Classic Boston sports bar, very near Fenway Park.  Baseball Tavern–great rooftop bar that actually overlooks Fenway Park.
    • Things to See: Fenway Park–take a tour, see a game, walk down Yawkey Way!  There are lots of fun things to do that are associated with the park and it’s a great way to spend an afternoon.

This list grows every time I visit my favorite city.  It’s in no way exhaustive, but it’s a good place to start!  Share your favorite Boston places in the comments–I’d love to know what you think is essential Boston!

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